DE69916733T3 - Stabile Komplexe schwer löslicher Substanzen - Google Patents
Stabile Komplexe schwer löslicher Substanzen Download PDFInfo
- Publication number
- DE69916733T3 DE69916733T3 DE69916733T DE69916733T DE69916733T3 DE 69916733 T3 DE69916733 T3 DE 69916733T3 DE 69916733 T DE69916733 T DE 69916733T DE 69916733 T DE69916733 T DE 69916733T DE 69916733 T3 DE69916733 T3 DE 69916733T3
- Authority
- DE
- Germany
- Prior art keywords
- compound
- water
- anionic polymer
- insoluble
- polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000126 substance Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 220
- 229920000642 polymer Polymers 0.000 claims description 71
- 229920006318 anionic polymer Polymers 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 62
- 239000002904 solvent Substances 0.000 claims description 30
- 239000008194 pharmaceutical composition Substances 0.000 claims description 26
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 25
- 229920003134 Eudragit® polymer Polymers 0.000 claims description 23
- 230000009477 glass transition Effects 0.000 claims description 22
- 238000001556 precipitation Methods 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 14
- 239000012530 fluid Substances 0.000 claims description 13
- 239000011159 matrix material Substances 0.000 claims description 12
- 230000001225 therapeutic effect Effects 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000006185 dispersion Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 239000002244 precipitate Substances 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 238000001694 spray drying Methods 0.000 claims description 7
- 229920003135 Eudragit® L 100-55 Polymers 0.000 claims description 6
- GDCRSXZBSIRSFR-UHFFFAOYSA-N ethyl prop-2-enoate;2-methylprop-2-enoic acid Chemical group CC(=C)C(O)=O.CCOC(=O)C=C GDCRSXZBSIRSFR-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 5
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims description 5
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 235000019441 ethanol Nutrition 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 4
- 230000008020 evaporation Effects 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229920003141 Eudragit® S 100 Polymers 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 230000001419 dependent effect Effects 0.000 claims description 3
- 229920000831 ionic polymer Polymers 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- -1 polyethylene Polymers 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 2
- 229920000623 Cellulose acetate phthalate Polymers 0.000 claims description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 2
- 229940081734 cellulose acetate phthalate Drugs 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- 229920002721 polycyanoacrylate Polymers 0.000 claims description 2
- 229940100467 polyvinyl acetate phthalate Drugs 0.000 claims description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- YIXSKDRXJTZCHT-UHFFFAOYSA-N 2-acetylbutanedioic acid Chemical compound CC(=O)C(C(O)=O)CC(O)=O YIXSKDRXJTZCHT-UHFFFAOYSA-N 0.000 claims 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 1
- FMTQGBMMIVVKSN-UHFFFAOYSA-N acetic acid;terephthalic acid Chemical compound CC(O)=O.OC(=O)C1=CC=C(C(O)=O)C=C1 FMTQGBMMIVVKSN-UHFFFAOYSA-N 0.000 claims 1
- 229940081735 acetylcellulose Drugs 0.000 claims 1
- 150000001449 anionic compounds Chemical class 0.000 claims 1
- 229920002301 cellulose acetate Polymers 0.000 claims 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 239000013557 residual solvent Substances 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 238000002441 X-ray diffraction Methods 0.000 description 17
- 239000002245 particle Substances 0.000 description 11
- 239000003814 drug Substances 0.000 description 8
- 238000000634 powder X-ray diffraction Methods 0.000 description 8
- 239000007962 solid dispersion Substances 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- 229940079593 drug Drugs 0.000 description 7
- 229920001993 poloxamer 188 Polymers 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HQPMKSGTIOYHJT-UHFFFAOYSA-N ethane-1,2-diol;propane-1,2-diol Chemical compound OCCO.CC(O)CO HQPMKSGTIOYHJT-UHFFFAOYSA-N 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 229920003139 Eudragit® L 100 Polymers 0.000 description 5
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000000825 pharmaceutical preparation Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 4
- 238000009474 hot melt extrusion Methods 0.000 description 4
- 238000003801 milling Methods 0.000 description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229920001477 hydrophilic polymer Polymers 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 238000012792 lyophilization process Methods 0.000 description 3
- 238000010951 particle size reduction Methods 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 238000001238 wet grinding Methods 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000000975 co-precipitation Methods 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012943 hotmelt Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 229940127557 pharmaceutical product Drugs 0.000 description 2
- 230000036470 plasma concentration Effects 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920003169 water-soluble polymer Polymers 0.000 description 2
- 0 CC*c(cc1)cc2c1C(C(C(C)=O)=C(C(*)=O)C1=C*(C*)c3c1cccc3)=C*2C Chemical compound CC*c(cc1)cc2c1C(C(C(C)=O)=C(C(*)=O)C1=C*(C*)c3c1cccc3)=C*2C 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007894 caplet Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000008041 oiling agent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dermatology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10133698P | 1998-09-22 | 1998-09-22 | |
| US101336P | 1998-09-22 | ||
| US13653199P | 1999-05-28 | 1999-05-28 | |
| US136531P | 1999-05-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE69916733D1 DE69916733D1 (de) | 2004-06-03 |
| DE69916733T2 DE69916733T2 (de) | 2005-03-31 |
| DE69916733T3 true DE69916733T3 (de) | 2009-09-24 |
Family
ID=26798138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69916733T Expired - Lifetime DE69916733T3 (de) | 1998-09-22 | 1999-09-13 | Stabile Komplexe schwer löslicher Substanzen |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US6350786B1 (OSRAM) |
| EP (1) | EP0988863B2 (OSRAM) |
| JP (5) | JP2000095708A (OSRAM) |
| KR (1) | KR100362019B1 (OSRAM) |
| CN (1) | CN1201821C (OSRAM) |
| AR (2) | AR022096A1 (OSRAM) |
| AT (1) | ATE265232T1 (OSRAM) |
| AU (1) | AU770745B2 (OSRAM) |
| BR (1) | BR9904283A (OSRAM) |
| CA (1) | CA2282906C (OSRAM) |
| CO (1) | CO5140077A1 (OSRAM) |
| CZ (1) | CZ300215B6 (OSRAM) |
| DE (1) | DE69916733T3 (OSRAM) |
| DK (1) | DK0988863T4 (OSRAM) |
| ES (1) | ES2218918T5 (OSRAM) |
| HR (1) | HRP990287B1 (OSRAM) |
| HU (1) | HU228341B1 (OSRAM) |
| ID (1) | ID24034A (OSRAM) |
| IL (1) | IL131957A (OSRAM) |
| MA (1) | MA26692A1 (OSRAM) |
| MY (1) | MY124377A (OSRAM) |
| NO (1) | NO326928B1 (OSRAM) |
| NZ (1) | NZ337884A (OSRAM) |
| PE (1) | PE20001049A1 (OSRAM) |
| PL (1) | PL202757B1 (OSRAM) |
| PT (1) | PT988863E (OSRAM) |
| RS (1) | RS50193B (OSRAM) |
| RU (1) | RU2240827C2 (OSRAM) |
| SG (1) | SG97131A1 (OSRAM) |
| SI (1) | SI0988863T2 (OSRAM) |
| TR (1) | TR199902324A3 (OSRAM) |
| TW (1) | TWI234465B (OSRAM) |
Families Citing this family (94)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE400252T1 (de) | 1999-02-10 | 2008-07-15 | Pfizer Prod Inc | Pharmazeutische feste dispersionen |
| US6440959B1 (en) * | 1999-04-21 | 2002-08-27 | Hoffman-La Roche Inc. | Pyrazolobenzodiazepines |
| AR033651A1 (es) * | 1999-10-01 | 2004-01-07 | Hoffmann La Roche | Derivados de pirimidina-2,4,6-triona, composiciones farmaceuticas que contienen dichos compuestos y el empleo de los mismos para la manufactura de un medicamento |
| US6313143B1 (en) * | 1999-12-16 | 2001-11-06 | Hoffmann-La Roche Inc. | Substituted pyrroles |
| AU2001255438B2 (en) * | 2000-05-16 | 2005-03-24 | Ortho-Mcneil Pharmaceutical, Inc. | Process for coating medical devices using super-critical carbon dioxide |
| US6469179B1 (en) | 2000-10-03 | 2002-10-22 | Hoffmann-La Roche Inc. | Amorphous form of cell cycle inhibitor having improved solubility and bioavailability |
| US6482847B2 (en) | 2000-10-03 | 2002-11-19 | Hoffmann-La Roche Inc. | Amorphous form of cell cycle inhibitor having improved solubility and bioavailability |
| US7193084B2 (en) | 2000-12-22 | 2007-03-20 | Baxter International Inc. | Polymorphic form of itraconazole |
| US20050048126A1 (en) | 2000-12-22 | 2005-03-03 | Barrett Rabinow | Formulation to render an antimicrobial drug potent against organisms normally considered to be resistant to the drug |
| US6607784B2 (en) | 2000-12-22 | 2003-08-19 | Baxter International Inc. | Microprecipitation method for preparing submicron suspensions |
| US9700866B2 (en) | 2000-12-22 | 2017-07-11 | Baxter International Inc. | Surfactant systems for delivery of organic compounds |
| US8067032B2 (en) | 2000-12-22 | 2011-11-29 | Baxter International Inc. | Method for preparing submicron particles of antineoplastic agents |
| US6951656B2 (en) | 2000-12-22 | 2005-10-04 | Baxter International Inc. | Microprecipitation method for preparing submicron suspensions |
| US6884436B2 (en) | 2000-12-22 | 2005-04-26 | Baxter International Inc. | Method for preparing submicron particle suspensions |
| US6977085B2 (en) | 2000-12-22 | 2005-12-20 | Baxter International Inc. | Method for preparing submicron suspensions with polymorph control |
| US6548531B2 (en) | 2001-02-09 | 2003-04-15 | Hoffmann-La Roche Inc. | Method for cancer therapy |
| US6716845B2 (en) * | 2001-03-30 | 2004-04-06 | Hoffmann-La Roche Inc. | Barbituric acid derivatives |
| ES2305250T3 (es) * | 2001-05-30 | 2008-11-01 | Csir | Procedimiento de encapsulacion de una sustancia activa. |
| US20030044514A1 (en) * | 2001-06-13 | 2003-03-06 | Richard Robert E. | Using supercritical fluids to infuse therapeutic on a medical device |
| WO2002102373A1 (en) * | 2001-06-15 | 2002-12-27 | F. Hoffmann-La Roche Ag | Method for administration of cancer therapeutic |
| WO2003000292A1 (en) | 2001-06-22 | 2003-01-03 | Pfizer Products Inc. | Pharmaceutical compositions comprising low-solubility and/or acid-sensitive drugs and neutralized acidic polymers |
| BR0210518A (pt) | 2001-06-22 | 2004-06-22 | Pfizer Prod Inc | Composições farmacêuticas de dispersões de drogas e polìmeros neutros |
| US20060003012A9 (en) | 2001-09-26 | 2006-01-05 | Sean Brynjelsen | Preparation of submicron solid particle suspensions by sonication of multiphase systems |
| CA2461349C (en) | 2001-09-26 | 2011-11-29 | Baxter International Inc. | Preparation of submicron sized nanoparticles via dispersion and solvent or liquid phase removal |
| US7112340B2 (en) | 2001-10-19 | 2006-09-26 | Baxter International Inc. | Compositions of and method for preparing stable particles in a frozen aqueous matrix |
| US20030139373A1 (en) * | 2001-11-20 | 2003-07-24 | Breimer Lars Holger | Method for cancer therapy |
| PT1469833T (pt) * | 2002-02-01 | 2021-07-13 | Bend Res Inc | Método para produzir dispersões de fármaco amorfo sólido seco por pulverização homogéneas utilizando aparelho de secagem por pulverização modificado |
| CN1681479A (zh) | 2002-08-12 | 2005-10-12 | 辉瑞产品公司 | 半有序药物和聚合物的药物组合物 |
| DE10351087A1 (de) * | 2003-10-31 | 2005-05-25 | Bayer Technology Services Gmbh | Feste Wirkstoff-Formulierung |
| WO2005046697A1 (ja) * | 2003-11-14 | 2005-05-26 | Ajinomoto Co., Inc. | フェニルアラニン誘導体の徐放性経口投与製剤 |
| KR101118930B1 (ko) * | 2003-11-14 | 2012-03-14 | 아지노모토 가부시키가이샤 | 페닐알라닌 유도체의 고체 분산체 또는 고체 분산체 의약제제 |
| JP4787240B2 (ja) * | 2004-04-01 | 2011-10-05 | ユニベルシテ・ド・リエージュ | ピリミジン−２，４，６−トリオンのシクロデキストリン包接複合体 |
| AR049915A1 (es) * | 2004-06-14 | 2006-09-13 | Anacor Pharmaceuticals Inc | Compuestos con contenido de boro y metodos de uso de los mismos |
| WO2006062980A2 (en) * | 2004-12-07 | 2006-06-15 | Nektar Therapeutics | Stable non-crystalline formulation comprising tiagabine |
| EP1839650A1 (en) * | 2004-12-28 | 2007-10-03 | Eisai R&D Management Co., Ltd. | Quick disintegration tablet and method of producing the same |
| CA2605214C (en) | 2004-12-31 | 2016-07-12 | Reddy Us Therapeutics, Inc. | Benzylamine derivatives as cetp inhibitors |
| US8604055B2 (en) | 2004-12-31 | 2013-12-10 | Dr. Reddy's Laboratories Ltd. | Substituted benzylamino quinolines as cholesterol ester-transfer protein inhibitors |
| EP1843798A2 (en) * | 2005-01-27 | 2007-10-17 | Corium International Inc., | Hydrophylic biocompatible adhesive formulations and uses |
| EP1690528A1 (de) * | 2005-02-11 | 2006-08-16 | Abbott GmbH & Co. KG | Herstellung von Dosierungsformen mit einer festen Dispersion eines mikrokristallinen Wirkstoffs |
| US20080274192A1 (en) * | 2005-05-19 | 2008-11-06 | Pfizer Inc. | Pharmaceutical Compositions Comprising an Amorphous Form of a Vegf-R-Inhibitor |
| EP1767194A1 (de) * | 2005-06-09 | 2007-03-28 | Helm AG | Verfahren zur Herstellung von Adsorbaten des Drospirenons |
| PT1893612E (pt) * | 2005-06-22 | 2011-11-21 | Plexxikon Inc | Derivados de pirrolo [2,3-b]piridina como inibidores de proteína quinase |
| US20080031944A1 (en) * | 2006-08-04 | 2008-02-07 | Cima Labs Inc. | Stabilization of lorazepam |
| CL2007002331A1 (es) * | 2006-08-10 | 2008-04-18 | Cipla Ltd | Composicion oral solida que comprede uno o mas farmacos antirretrovirales y al menos un polimero insoluble en agua, en relacion aproximadamente 1:1 hasta 1:6; proceso de elaboracion; y uso para el tratamiento del vih. |
| US20080107725A1 (en) * | 2006-10-13 | 2008-05-08 | Albano Antonio A | Pharmaceutical Solid Dosage Forms Comprising Amorphous Compounds Micro-Embedded in Ionic Water-Insoluble Polymers |
| WO2008063888A2 (en) | 2006-11-22 | 2008-05-29 | Plexxikon, Inc. | Compounds modulating c-fms and/or c-kit activity and uses therefor |
| WO2008079909A1 (en) * | 2006-12-21 | 2008-07-03 | Plexxikon, Inc. | Pyrrolo [2,3-b] pyridines as kinase modulators |
| PE20121126A1 (es) * | 2006-12-21 | 2012-08-24 | Plexxikon Inc | Compuestos pirrolo [2,3-b] piridinas como moduladores de quinasa |
| WO2008081829A1 (ja) | 2006-12-27 | 2008-07-10 | Astellas Pharma Inc. | 難水溶性薬物の溶解性維持用アミノアルキルメタアクリレートコポリマーｅ |
| JP2010526848A (ja) * | 2007-05-11 | 2010-08-05 | エフ．ホフマン−ラ ロシュ アーゲー | 難溶性薬物用の医薬組成物 |
| US8426467B2 (en) | 2007-05-22 | 2013-04-23 | Baxter International Inc. | Colored esmolol concentrate |
| US8722736B2 (en) | 2007-05-22 | 2014-05-13 | Baxter International Inc. | Multi-dose concentrate esmolol with benzyl alcohol |
| EP1997479A1 (en) * | 2007-05-31 | 2008-12-03 | Helm AG | Stabilized amorphous candesartan cilexetil compositions for oral administration |
| AU2008276063B2 (en) | 2007-07-17 | 2013-11-28 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| CN101896161A (zh) * | 2007-10-19 | 2010-11-24 | 普渡（大学）研究基金 | 结晶化合物的固体制剂 |
| US8632805B2 (en) * | 2008-06-20 | 2014-01-21 | Mutual Pharmaceutical Company, Inc. | Controlled-release formulations, method of manufacture, and use thereof |
| US7794750B2 (en) * | 2008-06-20 | 2010-09-14 | Mutual Pharmaceutical Company, Inc. | Controlled-release formulations, method of manufacture, and use thereof |
| US20100099696A1 (en) * | 2008-10-16 | 2010-04-22 | Anthony Edward Soscia | Tamper resistant oral dosage forms containing an embolizing agent |
| KR20100073454A (ko) * | 2008-12-23 | 2010-07-01 | 국립암센터 | 트란스글루타미나제 억제제로 사용되는 신규한 피라졸로디아제핀계 화합물, 이의 제조방법 및 이를 포함하는 조성물 |
| JP5511942B2 (ja) * | 2009-04-03 | 2014-06-04 | エフ ホフマン−ラ ロッシュ アクチェン ゲゼルシャフト | 組成物及びその使用 |
| US8329724B2 (en) | 2009-08-03 | 2012-12-11 | Hoffmann-La Roche Inc. | Process for the manufacture of pharmaceutically active compounds |
| EP2496086B1 (en) | 2009-11-06 | 2017-05-31 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| EP2581084A4 (en) * | 2010-05-31 | 2014-06-25 | Astellas Pharma Inc | SOLID DISPERSION COMPRISING A TRIAZOLE COMPOUND |
| SI2672967T1 (sl) | 2011-02-07 | 2018-12-31 | Plexxikon Inc. | Spojine in postopki za kinazno modulacijo in indikacije zanjo |
| BR112013021030A2 (pt) | 2011-02-17 | 2016-10-11 | Hoffmann La Roche | processo para cristalização controlada de um ingrediente farmacêutico ativo a partir de estado líquido super-refrigerado por extrusão por fusão a quente |
| AR085279A1 (es) | 2011-02-21 | 2013-09-18 | Plexxikon Inc | Formas solidas de {3-[5-(4-cloro-fenil)-1h-pirrolo[2,3-b]piridina-3-carbonil]-2,4-difluor-fenil}-amida del acido propano-1-sulfonico |
| AP3310A (en) | 2011-06-20 | 2015-06-30 | Lundbeck & Co As H | Deuterated 1-piperazino-3-phenyl indanes for treatment of schizophrenia |
| JP5964965B2 (ja) | 2011-08-18 | 2016-08-03 | ドクター レディズ ラボラトリーズ リミテッド | コレステリルエステル転送タンパク質（ｃｅｔｐ）インヒビターとしての置換複素環式アミン化合物 |
| WO2013037396A1 (en) * | 2011-09-12 | 2013-03-21 | Bioneer A/S | Solution of polymer in api for a solid dosage form |
| AU2012313971B2 (en) | 2011-09-27 | 2016-09-29 | Dr. Reddy's Laboratories, Ltd. | 5 - benzylaminomethyl - 6 - aminopyrazolo [3, 4 -b] pyridine derivatives as cholesteryl ester -transfer protein (CETP) inhibitors useful for the treatment of atherosclerosis |
| EP2765990B1 (en) | 2011-10-14 | 2017-09-06 | Array Biopharma, Inc. | Solid dispersion |
| RU2018138976A (ru) * | 2012-03-23 | 2018-12-06 | Эррэй Биофарма Инк. | Лечение рака головного мозга |
| US20140128431A1 (en) | 2012-04-03 | 2014-05-08 | Hoffmann-Laroche Inc. | Pharmaceutical composition with improved bioavailability, safety and tolerability |
| EP2649989B1 (en) | 2012-04-13 | 2017-10-18 | King Saud University | Method for preparing a solid dispersion, solid dispersion obtained thereby and use thereof |
| US9150570B2 (en) | 2012-05-31 | 2015-10-06 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
| JO3339B1 (ar) * | 2012-09-11 | 2019-03-13 | Shanghai Inst Pharmaceutical Ind | شكل مستقر غير متبلور من الأغوميلاتين وعملية تحضيره والتركيبات الدوائية التي تحتوي عليه |
| US20170071930A1 (en) | 2012-11-19 | 2017-03-16 | Dr. Reddy's Laboratories Ltd. | Pharmaceutical compositions of cetp inhibitors |
| EP2934486A2 (en) * | 2012-12-20 | 2015-10-28 | Kashiv Pharma, LLC | Orally disintegrating tablet formulation for enhanced bioavailability |
| KR101737250B1 (ko) | 2013-01-22 | 2017-05-17 | 에프. 호프만-라 로슈 아게 | 개선된 생체이용률을 갖는 약학 조성물 |
| TWI615157B (zh) | 2013-02-06 | 2018-02-21 | 大塚製藥股份有限公司 | 包括不定形西洛他唑的固體分散劑 |
| WO2015038376A1 (en) * | 2013-09-11 | 2015-03-19 | 3M Innovative Properties Company | Coating compositions, dental structures thereof and methods for generating contrast |
| EP3076951B1 (en) * | 2013-12-05 | 2020-09-30 | Celal Albayrak | Process for the production of drug formulations for oral administration |
| PT107846B (pt) * | 2014-08-01 | 2019-03-22 | Hovione Farm S A | Produção de nano- partículas de dispersões sólidas amorfas por co-precipitação controlada |
| RU2017144222A (ru) * | 2015-05-29 | 2019-07-02 | Сан Фармасьютикал Индастриз Лимитед | Фармацевтическая пероральная композиция изотретиноина |
| SMT202500245T1 (it) | 2016-12-13 | 2025-07-22 | Transthera Sciences Nanjing Inc | Composto inibitore multi-chinasi, forma cristallina e suo utilizzo |
| CA3060407A1 (en) | 2017-04-28 | 2018-11-01 | Seattle Genetics, Inc. | Treatment of her2 positive cancers |
| KR102082775B1 (ko) * | 2017-05-02 | 2020-02-28 | 주식회사 삼양바이오팜 | 수용해도 및 생체이용율이 개선된 조성물 |
| RU2725879C2 (ru) * | 2018-07-26 | 2020-07-07 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Казанский Государственный медицинский университет" Министерства здравоохранения Российской Федерации | Интерполимерный носитель для пероральных систем контролируемой доставки активных фармацевтических ингредиентов |
| US11535600B2 (en) | 2018-12-03 | 2022-12-27 | H. Lundbeck A/S | Prodrugs of 4-((1R,3S)-6-chloro-3-phenyl-2,3-dihydro-1H-inden-1-yl)-1,2,2-trimethylpiperazine and 4-((1R,3S)-6-chloro-3-(phenyl-d5)-2,3-dihydro-1H-inden-1-yl)-2,2-dimethyl-1-(methyl-d3)piperazine |
| IL294928A (en) * | 2020-01-24 | 2022-09-01 | Nanocopoeia Llc | Amorphous solid dispersions of dasatinib and uses thereof |
| AU2021212258A1 (en) | 2020-01-31 | 2022-09-29 | Flex Pharma, Llc | Amorphous nilotinib microparticles and uses thereof |
| JP7705715B2 (ja) | 2020-03-03 | 2025-07-10 | デクセリアルズ株式会社 | 画像表示装置の製造方法 |
| EP4142699A1 (en) | 2020-04-30 | 2023-03-08 | Nanocopoeia LLC | Orally disintegrating tablet comprising amorphous solid dispersion of nilotinib |
| US11980619B2 (en) | 2021-07-28 | 2024-05-14 | Nanocopoeia, Llc | Pharmaceutical compositions and crushable tablets including amorphous solid dispersions of dasatinib and uses |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51118816A (en) * | 1975-04-08 | 1976-10-19 | Meiji Seika Kaisha Ltd | A process for stabilizing non-crystalloidal solid |
| US4344934A (en) * | 1978-11-20 | 1982-08-17 | American Home Products Corporation | Therapeutic compositions with enhanced bioavailability |
| PT83812B (en) * | 1985-11-27 | 1988-03-15 | Syntex Inc | Process for preparing amorphous benzimidazole derivatives |
| GB8608080D0 (en) * | 1986-04-02 | 1986-05-08 | Fujisawa Pharmaceutical Co | Solid dispersion composition |
| NZ227850A (en) † | 1988-02-10 | 1991-11-26 | Hoffmann La Roche | Indole substituted pyrrole derivatives; preparatory process and medicaments for use against inflammatory immunological, bronchopulmonary or vascular disorders |
| JP2528706B2 (ja) † | 1988-05-30 | 1996-08-28 | ゼリア新薬工業株式会社 | ジヒドロピリジン化合物の製剤組成物 |
| USRE36736E (en) | 1989-02-06 | 2000-06-13 | Hoffman-La Roche Inc. | Substituted pyrroles |
| JPH0729926B2 (ja) † | 1989-07-25 | 1995-04-05 | 大塚製薬株式会社 | 易吸収性製剤用組成物 |
| US5399363A (en) | 1991-01-25 | 1995-03-21 | Eastman Kodak Company | Surface modified anticancer nanoparticles |
| ATE159426T1 (de) † | 1991-04-16 | 1997-11-15 | Nippon Shinyaku Co Ltd | Verfahren zur herstellung einer festen dispersion |
| US5281420A (en) | 1992-05-19 | 1994-01-25 | The Procter & Gamble Company | Solid dispersion compositions of tebufelone |
| TW493991B (en) | 1995-05-08 | 2002-07-11 | Novartis Ag | Pharmaceutical composition for oral administration of active agent having low water solubility and process for preparation of the same |
| GB9511220D0 (en) † | 1995-06-02 | 1995-07-26 | Glaxo Group Ltd | Solid dispersions |
| BE1009856A5 (fr) * | 1995-07-14 | 1997-10-07 | Sandoz Sa | Composition pharmaceutique sous la forme d'une dispersion solide comprenant un macrolide et un vehicule. |
| WO1997004782A1 (en) * | 1995-07-26 | 1997-02-13 | Kyowa Hakko Kogyo Co., Ltd. | Solid dispersion or solid dispersion preparation of xanthine derivatives |
| WO1997008950A1 (en) † | 1995-09-07 | 1997-03-13 | Fuisz Technologies, Ltd. | System for rendering substantially non-dissoluble bio-affecting agents bio-available |
| DE19548624A1 (de) | 1995-12-23 | 1997-06-26 | Boehringer Mannheim Gmbh | Neue Barbitursäure-Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| JPH09208459A (ja) * | 1996-02-07 | 1997-08-12 | Eisai Co Ltd | 溶解性を改良した製剤 |
| JP3737518B2 (ja) | 1996-03-12 | 2006-01-18 | ピージー−ティーエックスエル カンパニー， エル．ピー． | 水溶性パクリタキセルプロドラッグ |
| EP0954288B1 (en) * | 1996-06-28 | 2004-08-11 | Schering Corporation | Solid solution of an antifungal agent with enhanced bioavailability |
| PE91598A1 (es) | 1996-07-29 | 1998-12-24 | Hoffmann La Roche | Pirroles sustituidos |
| US6229011B1 (en) | 1997-08-22 | 2001-05-08 | Hoffman-La Roche Inc. | N-aroylphenylalanine derivative VCAM-1 inhibitors |
| CA2322689C (en) | 1998-03-17 | 2008-11-25 | F. Hoffmann-La Roche Ag | Substituted bisindolymaleimides for the inhibition of cell proliferation |
-
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- 1999-09-21 JP JP11267142A patent/JP2000095708A/ja not_active Withdrawn
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- 1999-09-22 KR KR1019990041130A patent/KR100362019B1/ko not_active Expired - Lifetime
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